A simple preparation of 2,3,4,6-tetra-o-acyl-gluco-, galacto- and mannopyranoses and relevant theoretical study.

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Zerong Daniel WangMinghong Liu

Abstract

The deacylation of glucose, galactose and mannose pentaacetates, galactose and mannose penta(3-bromo)benzoates, as well as the dealkylation of 2,3,4,6-tetra-O-acetyl and 2,3,4,6-tetra-O-(3-bromo)benzoyl methyl alpha-D-glucopyranosides have been studied. In addition, a computational study on the deacylation of beta-D-glucose pentaacetate has been carried out with density functional theory (B3LYP/6-31G*). The anomeric effect during deacetylation and dealkylation has been clearly demonstrated in both experimental and computational results.

References

Oct 25, 2001·The Journal of Organic Chemistry·Jongheon ShinYoun Jung Cho
Dec 11, 2003·Journal of the American Chemical Society·Nicolas LaurentJohn W Goodby
Mar 27, 2004·Journal of Natural Products·Philippe JoubertBrigitte S Sangwan-Norreel
Jul 29, 2004·Organic & Biomolecular Chemistry·Robert R FranceJay D Wadhawan
Dec 28, 2005·Journal of Natural Products·Wei LiTamotsu Nikaido
Aug 29, 2006·Journal of Natural Products·Yuko OgawaKyoko Ishiguro
Nov 17, 2007·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Zerong Daniel WangSamia Sheikh
Mar 5, 2008·Journal of Natural Products·Hiroe KikuzakiNobuji Nakatani
Mar 17, 2009·Journal of Natural Products·Sergei S ZhokhovAnders Broberg

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Citations

Nov 4, 2011·Bioorganic & Medicinal Chemistry Letters·Amy CammarataDonna M Neumann

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Methods Mentioned

BETA
glycosylation
deacylation
column chromatography
deacylations
NMR

Software Mentioned

Gaussian

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